Collective asymmetric synthesis of (-)-Antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert- butanesulfinamide as a chiral auxiliary

Journal of Organic Chemistry

Volumn 79, Issue 8, 2014, Pages 3348-3357

  Zheng, Yanlong ^a   Liu, Yuxiu ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN COMPOUNDS; SUBSTITUTION REACTIONS;

ASYMMETRIC ALLYLATION; ASYMMETRIC SYNTHESIS; CHIRAL AUXILIARIES; CYCLOISOMERIZATION REACTIONS; HOMOALLYLIC AMINES; PIPERIDINE RINGS; REACTION SEQUENCES; RING-CLOSING METATHESIS REACTIONS;

REACTION INTERMEDIATES;

ALKALOID; ANTOFINE; CRYPTOPLEURINE; PHENANTHRENE; TYLOCREBRINE; TYLOPHORINE; UNCLASSIFIED DRUG;

ALLYLATION; ANNULATION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; DRUG SYNTHESIS; HYDROBORATION; HYDROGENOLYSIS; OXIDATION; RING CLOSING METATHESIS; SUBSTITUTION REACTION;

ALKALOIDS; BUTANES; INDOLES; INDOLIZINES; ISOMERISM; MOLECULAR STRUCTURE; PHENANTHRENES; PHENANTHROLINES; STEREOISOMERISM; SULFONAMIDES;

EID: 84898936888     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500013e     Document Type: Article

References (50)

1. Gellert, E. J. Nat. Prod. 1982, 45, 50-73
2. Li, Z. G.; Jin, Z.; Huang, R. Q. Synthesis 2001, 2365-2378
3. Chemler, S. R. Curr. Bioact. Compd. 2009, 5, 2-19 and references therein
4. Krishna, R. B.; Balaji, M.; Uma, R. P.; Sailaja, G.; Vaidyanath, K.; Narasimha, G. Afr. J. Biochem. Res. 2009, 3, 393-397
5. Ganguly, T.; Sainis, K. B. Phytomedicine 2001, 8, 348-355
6. Yadav, M.; Dwivedi, P.; Singh, P.; Singh, V. K. Indian J. Plant Physiol. 2010, 15, 297-301
7. You, X.; Pan, M.; Gao, W.; Shiah, H. S.; Tao, J.; Zhang, D.; Koumpouras, F.; Wang, S.; Zhao, H.; Madri, J. A.; Baker, D.; Cheng, Y. C.; Yin, Z. Arthritis Rheum. 2006, 54, 877-886
8. Yang, C. W.; Chen, W. L.; Wu, P. L.; Tseng, H. Y.; Lee, S. J. Mol. Pharmacol. 2006, 69, 749-758
9. Min, H. Y.; Song, S. H.; Lee, B.; Kim, S. H.; Lee, S. K. Chem. Biodiversity 2010, 7, 409-413
10. Lee, Y. Z.; Huang, C. W.; Yang, C. W.; Hsu, H. Y.; Kang, I. J.; Chao, Y. S.; Chen, I. S.; Chang, H. Y.; Lee, S. J. Planta Med. 2011, 77, 1932-1938
11. Wang, K. L.; Su, B.; Wang, Z. W.; Wu, M.; Li, Z.; Hu, Y. N.; Wang, Q. M. J. Agric. Food. Chem. 2010, 58, 2703-2709
12. Suffness, M.; Douros, J. In Anticancer Agents Based on Natural Product Models; Cassady, J. M.; Douros, J. D., Eds.; Medicinal Chemistry Series, Vol. 16; Academic Press: London, 1980; pp 465-487.
13. Cui, M. B.; Song, H. J.; Feng, A. Z.; Wang, Z. W.; Wang, Q. M. J. Org. Chem. 2010, 75, 7018-7021
14. Pansare, S. V.; Lingampally, R.; Dyapa, R. Eur. J. Org. Chem. 2011, 12, 2235-2238
15. Mai, D. N.; Wolfe, J. P. J. Am. Chem. Soc. 2010, 132, 12157-12159
16. Zeng, W.; Chemler, S. R. J. Org. Chem. 2008, 73, 6045-6047
17. Kim, S.; Lee, J. K.; Lee, T. H.; Park, H. G.; Kim, D. Org. Lett. 2003, 5, 2703-2706
18. Yang, X.; Shi, Q.; Bastow, K. F.; Lee, K. H. Org. Lett. 2010, 12, 1416-1419
19. Stoye, A.; Opatz, T. Org. Lett. 2010, 12, 2140-2141
20. Niphakis, M. J.; Georg, G. I. Org. Lett. 2011, 13, 196-199
21. Kim, S.; Lee, T.; Lee, E.; Lee, J.; Fan, G. J.; Lee, S. K.; Kim, D. J. Org. Chem. 2004, 69, 3144-3149
22. Dumoulin, D.; Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P. Eur. J. Org. Chem. 2010, 10, 1943-1950
23. McIver, A.; Young, D. D.; Deiters, A. Chem. Commun. 2008, 39, 4750-4752
24. Bremmer, M. L.; Khatri, N. A.; Weinreb, S. M. J. Org. Chem. 1983, 48, 3661-3666
25. Su, B.; Chen, F. Z.; Wang, Q. M. J. Org. Chem. 2013, 78, 2775-2779
26. Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913-9914
27. Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883-8904
28. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995
29. Ferreira, F.; Botuha, C.; Chemla, F.; Pérez-Luna, A. Chem. Soc. Rev. 2009, 38, 1162-1186
30. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600-3740
31. Lin, G. Q.; Xu, M. H.; Zhong, Y. W.; Sun, X. W. Acc. Chem. Res. 2008, 41, 831-840
32. Sun, X. W.; Xu, M. H.; Lin, G. Q. Org. Lett. 2006, 8, 4979-4982
33. Sun, X. W.; Liu, M.; Xu, M. H.; Lin, G. Q. Org. Lett. 2008, 10, 1259-1262
34. Kolodney, G.; Sklute, G.; Perrone, S.; Knochel, P.; Marek, I. Angew. Chem., Int. Ed. 2007, 46, 9291-9294
35. Marvin, C. C.; Voight, E. A.; Suh, J. M.; Paradise, C. L.; Burke, S. D. J. Org. Chem. 2008, 73, 8452-8457
36. Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278-1284
37. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555-2563
38. Cui, L.; Li, C.; Zhang, L. Angew. Chem., Int. Ed. 2010, 49, 9178-9181
39. Bailey, P. D.; Beard, M. A.; Dang, H.; Phillips, T. R.; Price, R. A.; Whittaker, J. H. Tetrahedron Lett. 2008, 49, 2150-2153
40. Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 1956-1962
41. Felpin, F. X.; Lebreton, J. Eur. J. Org. Chem. 2003, 19, 3693-3712
42. Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077
43. Gellert, E.; Govindachari, T. R.; Lakshmikantham, M. V.; Ragade, I. S.; Rudzats, R.; Viswanathan, N. J. Chem. Soc. 1962, 189, 1008-1014
44. Wang, K. L.; Lü, M. Y.; Yu, A.; Zhu, X. Q.; Wang, Q. M. J. Org. Chem. 2009, 74, 935-938
45. Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264-6267
46. Mamane, V.; Hannen, P.; Fürstner, A. Chem. - Eur. J. 2004, 10, 4556-4575
47. Fürstner, A.; Kennedy, J. W. J. Chem. - Eur. J. 2006, 12, 7398-7410
48. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 18, 734-736
49. Kwon, Y.; Cho, H.; Kim, S. Org. Lett. 2013, 15, 920-923
50. Davies, K. A.; Abel, R. C.; Wulff, J. E. J. Org. Chem. 2009, 74, 3997-4000